Dyestuffs of the anthraquinone series



Patented Aug. 22, 1933 UNITED STATES PATENT OFFICE DYESTUFFS or THE ANTHRAQUINONE seams Paul Nawiasky and Otto Chrzescinski, Ludwigs hafen-on-the-Rhine,

Germany, assignors to General Aniline Works, Inc., New York, N.- Y;, a Corporation of Delaware 7 No Drawing. Application June 7, 1930, Serial No. 459,827, and in Germany June 14, 1929 5 Claims.

in which X,X and Y,Y stand for vicinal carbon atoms of anthraquinone radicles which may be substituted. The new dyestufis generally speaking possess excellent fastness properties and show an important technical deepening or displacement of shade in contrast to the products obtainable by the action of the corresponding aminoanthraquinones on lA dih-alogenanthraqui nones and subsequent action of acid condensing agents.

The following examples will further illustrate the nature of this invention, but the invention is not restricted to these examples. The parts are by weight.

Example 1 4 parts of the product obtainable by boiling 5.8-dichloro-1.2-benzanthraquinone and l-aminoanthraquinone in nitrobenzene in the presence of copper acetate, copper powder and sodium acetate are introduced at 100 centigrade into as olution of 8 .parts of aluminium chloride in 16 parts of pyridine prepared'while cooling The whole is then stirred at from 125 to 130 centigrade until the reaction is completed, when it is diluted with water and worked up in the usual manner, the crude dyestuff obtained being preferably purified by vatting and reprecipitation.

The new dyestufi probably corresponding to the formula:

is a dark brown powder which dissolves in sulphuric acid 'monohydrate giving a brown violet coloration and which dyes cotton from a warm red brown hydrosulphite vat powerful brown shades fast to chlorine and soaping and having excellent fastness properties.

Example 2 4 parts of the product obtainable by heating 6.8 parts of 1-amino-5 benzoylaminoanthraquinone with 3.5 parts of 5.8-dichloro-1.2-benzanthraquinone in nitrobenzene in the presence of sodium acetate and copper compounds, are treated with a solution of aluminium chloride invpyridine as described in Example 1 and are worked up in the same manner. A dyestuff probably corresponding to the formula:

dyestuff, which comprises heating a product corresponding to the formula:

0 H O so u o o o N-Ho O N-H O t i 1 with a solution of aluminium chloride in pyriis obtained in excellent yields which dissolves in dine. sulphuric acid giving a blue coloration and which 2. The vat dyestufl probably corresponding to dyes cotton from a warm red brown hydrosulthe formula: phite vat in beautiful pure brown shades.

By subjecting the reaction product from 1- amino-4-benzoylaminoanthraquinone and 5.8- dichloro-1.2-benzanthraquinone to the same reaction a dyestuff is obtained which dissolves in concentrated sulphuric acid giving a dark green O coloration and which dyes cotton from a warm red brown hydrosulphite vat powerful brown shades of good covering power and excellent fastness properties. It probably has the formula:

OnH5.00.HN \O I H5C6.0Q.HN/ Q the dyestufl'dlssolving in concentrated sulphuric acid giving a blue solution and dyeing cotton from a" red brown vat pure brown shades.

Q What we claim is:

1. A process for the production'of a new vat The vat dyestufi probabl y corresponding to the formula:

OsHLCOJIN NH O I O N-H O in which the anthraquinone radicles may be substituted in the alpha-positions by benzoylamino radlcles.

5. Vat dyestufls probably corresponding to the formula:

in which the anthraquinone radicles may be substituted in the alpha-positions by benzoylamino radicles, the dyestufis being soluble in concentrated sulphuric acid and dyeing cotton brown shades from red brown vats.

PAUL NAWIASKY.

O'I'IO CHRZESCINSKI. 

